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Now that I have been transplanted to Portland, we've been able to try a lot of the restaurants others have cited here, and you all are spot on. Among our favorites:
Ken's Artisan Bakery (breads, pastries, and especially their Monday night-only pizza)
Bunk Sandwiches (but also try Bunk Bar, which has most of the Bunk sandwich menu, plus a fine selection of beers)
Simpatico Dining Hall (never been disappointed, and always had interesting table mates, including from DC)
Beaker and Flask (creative drinks; we let the bartender decide what to serve us)
Happy Hours at places that do not skimp on the quality of food and drink (such as 21 Hoyt, Serrato, Clyde Common, Bar Mingo, Elephants)
Red Onion (authentic Thai, especially if you order off the special menu)
Wildwood (still good after many years)
Por Que No Taqueria (funky and friendly)
Olympic Provisions (for house-made charcouterie and anything porky; took an afternoon pork butchering class there and went home with 10 pounds of the most sublime peach-fed pork I have ever tasted)
Andina (a bit too trendy for our tastes, but good Peruvian-style food and drink)
The food cart scene is addicting (we’ve especially become fans of Koi Fusion)
Tabla (ethereal house-made pasta)
Local small-batch roasted coffees (Coava: a bit too ritualistic, but great roasts; Courier Coffee; Ristretto)
Still searching for a good Indian restaurant.
Other local treats are the beers, of course, and a growing distillery scene (an hour spent tasting at Clear Creek, the first to make a name for itself, is an hour well spent)
Most of our outings have been on the West Side where we live, and we need to expand our horizons more to the East Side. So many places; so little time.

Not quite your definition, but we formed an "ad hoc" communal table last week at Masala Art. Place was crowded. Two other couples and we were waiting in the bar area for two-tops to open up. The host said it would be awhile, but that he had a six-top in the front window area that would be free soon and that we could have it if we were willing to share. None of the couples knew each other, but we agreed to give it try; it worked out great. Engaging dining companions and easy conversationalists. Server handled it well. Fun experience. (Great food, too, of course.)

Next time you go to Buffalo, try the wings at Duff's (corner of Sheridan Drive and Millersport Highway, in suburban Amherst NY). Many Buffalonians believe them superior to Anchor Bar, which some say has jumped the shark. We have tried both often; Anchor has the history and atmosphere; Duff's has better sauce (and is closer to home).

We met the new fishmonger tonight--MJ Gimber--who introduced himself as we were leaving Happy Hour and picking up some fish for the weekend. Personable young man; told us he comes from the wholesale seafood business in NYC. Fish counter was splendidly stocked, including with some varieties of fish I had not seen there often and some at very attractive prices. He also was informative in offering cooking and serving suggestions. Looks like it will still be my favorite fish market.

Thanks for the hint on the Chelsea "Inn." We often stay at an even more rustic Chelsea "Lodge" on 20th Street. Sounds similar -- narrow flights of stairs to smallish rooms and a shared bath. One of our favorite breakfast excursions is just to walk down the street to La Bergamote Patisserie at the corner of 20th and 9th Avenue.

Get on their email list for coupons and also look for coupons mailed around the neighborhood. We usually receive a few coupons a month for $4-5 off on a large pizza, which brings the cost down quite a bit. Service at the Spring Valley location is often iffy; seems like they get overwhelmed at times. I found that if I am promised a pizza in 20 minutes, arrive on schedule, but have to wait a lot longer, I can express my disappointment and they will often throw in a free salad or cookie; one recent long delay resulted in a free pint of ice cream. On the other hand, they can be very accommodating: in a hurry tonight, I dumbly called the new Chevy Chase store instead of Spring Valley (I had been used to looking for the 202 area code on their website and did not realize there were now two DC stores). Of course, Spring Valley had no order for me to pick up, but they nonetheless hustled one in under 10 minutes and I went home happy.

Revisited some favorites and a new one in Chicago over the Labor Day weekend. Frontera Grill was as good as expected, but showing the effects of Chef Bayless’s media exposure with long lines and wait times, even on Thursday evening. Our seviche and queso fundido classico appetizers were excellent, especially the latter, which nicely balanced the cheese and the savory. Mains included poc chuc de puerco (orange-marinated, grill-seared pork with a killer habanero salsa that staff insisted on constantly warning me about whenever they passed the table) and a chicken enchilada with a deeply flavored mole sauce. After-dinner entertainment was watching through the window of the building down the street where Chef Bayless was directing a soft opening of a new venture, the XOCO café of Mexican street food (opens September 8).
We hadn’t been to Green Zebra for several years, but were not disappointed in its high-end vegetarian menu. Our variety of small plates included an elegant, creamy, melt-in-your mouth burrata with candied olive, lemon, fava beans, and tempura squash blossom; roasted beet salad with goat cheese croquettes, artichoke, and preserved lemon; poached egg with smoked potato puree that, had it not been vegetarian, you would have believed was laced with bacon; warm braised artichoke and bread salad with a paprika tomato sauce; heirloom tomato tortellini in a parmesan fennel broth; and a lobster mushroom crepe. I’ll definitely have to try to recreate the poached egg and smoked potato dish!
Went back to Avec, where we had a roasted eggplant crostini garnished with smoked corn kernels; a magnificently flavored and textured presentation of dates stuffed with chorizo in a piquillo pepper-tomato sauce; turkey and guanciale meatballs with an amatriciana sauce; and pan-fried lake trout with lemon aioli that reminded me of how good fresh Great Lakes fish were back in the pre-pollution 1950s. Happily, we also had delightful dining partners at the communal table. Having been there before, we arrived around 5:00 and were seated right away; by the time we left the line at the door was several dozen people deep.
Our new try was Salpicon, which had Mexican flavors that were not quite as exacting as Frontera, but was absent the attendant hassle. Appetizers of squash blossoms filled with goat cheese and jalapenos rellenos were excellent, with the jalapeno edging out because of the intensely flavored black bean sauce that came with it. Main dished included a perfectly cooked “tinga poblana” (pork tenderloin with chorizo and potatoes and a roasted tomato-chipotle sauce) and chiles rellenos (the pork-stuffed chile was A-plus; the cheese stuffed chile was marred by a heavy hand with the salt). Salpicon’s tequila menu is overwhelming for a novice like me, but would please aficionados, no doubt.

We thought Joe Fortes was overrated last time we were there; no better than a McCormick and Schmick or a Clydes rather than something uniquely Vancouveran. Bishop is reliable but may be showing its age. Loved Chambar (if you like mussels and Belgian beer). Vij is terrific. Always have enjoyed Raincity Grill. We're jealous of your trip; please report back!